Process for hydroxyalkylation of cyanoethylanilines

Abstract

A process is provided for hydroxyalkylation of cyanoethylanilines, which comprises reacting an alkylene oxide of the formula: ##STR1## wherein R 1 is selected from H, Cl, Br, OH, a lower alkyl group containing from 1 to about 4 carbon atoms, or phenyl with a cyanoethyl aniline in a molar ratio of from about 1:1 to about 2:1 in a reaction medium at a temperature of from about 40° C. to about 130° C. in the presence of an acid catalyst provided in an amount sufficient to catalyze said reaction to thereby provide the corresponding hydroxyalkylated cyanoethyl aniline.

What is claimed is: 
     
       1. A process for hydroxyalkylation of cyanoethylanilines which comprises reacting an alkylene oxide of the formula: ##STR6## wherein R 1  is selected from H, Cl, Br, OH, a lower alkyl group containing from 1 to about 4 carbon atoms, or phenyl with a cyanoethylaniline in a molar ratio of from about 1:1 to about 2:1 in a reaction medium at a temperature of less than 100° C. in the presence of an acid catalyst provided in an amount sufficient to catalyze said reaction to thereby provide the corresponding hydroxyalkylated cyanoethylaniline. 
     
     
       2. The process of claim 1 wherein said cyanoethylanilines are represented by the following structural formula: ##STR7## wherein R 2  is selected from H, Cl, Br, OH, a lower alkyl group containing from 1 to about 4 carbon atoms, or phenyl; and R 3 , R 4  and R 5  are each independently selected from H, a lower alkyl group containing from 1 to about 4 carbon atoms, halogen, NO 2 , OH, a lower alkoxy group containing from 1 to about 4 carbon atoms, and NHCOR 6  where R 6  is H or a lower alkyl group containing from 1 to about 4 carbon atoms. 
     
     
       3. The process of claim 1 wherein said reaction is performed for from about 0.2 to about 8 hours. 
     
     
       4. The process of claim 1 wherein said reaction is performed in the absence of a solvent. 
     
     
       5. The process of claim 1 wherein said reaction is performed in the presence of a solvent selected from water, cycloaliphatic ethers and high boiling hydrocarbons. 
     
     
       6. The process of claim 1 wherein said acid catalyst is an organic acid. 
     
     
       7. The process of claim 6 wherein said organic acid is selected from acetic, formic, propionic, paratoluenesulfonic or methanesulfonic acids. 
     
     
       8. The process of claim 7 wherein said acid is acetic acid. 
     
     
       9. The process of claim 1 wherein said acid catalyst is present in an amount of from about 1 percent to about 30 percent by weight. 
     
     
       10. The process of claim 1 wherein said acid catalyst is a Lewis acid. 
     
     
       11. The process of claim 1 wherein said Lewis acid is zinc chloride. 
     
     
       12. The process of claim 1 wherein said acid catalyst is a mineral acid catalyst.